JPH03135966A - 二酸化硫黄吸収剤として用いるピペラジノンの製造方法 - Google Patents

二酸化硫黄吸収剤として用いるピペラジノンの製造方法

Info

Publication number: JPH03135966A
Authority: JP; Japan
Prior art keywords: piperazinone; product; reaction; compound; group
Prior art date: 1989-10-06
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP2266516A

Other languages

English (en)

Japanese (ja)

Inventor

Steven H Christiansen

スティーブン　エイチ．クリスチャンセン

Chang Dane

デイン　チャング

David A Wilson

デビッド　エー．ウィルソン

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Dow Chemical Co

Original Assignee

Dow Chemical Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1989-10-06

Filing date

1990-10-05

Publication date

1991-06-10

1990-10-05 Application filed by Dow Chemical Co filed Critical Dow Chemical Co

1991-06-10 Publication of JPH03135966A publication Critical patent/JPH03135966A/ja

Status Pending legal-status Critical Current

Links

IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 title claims abstract description 26
230000002745 absorbent Effects 0.000 title claims abstract description 15
239000002250 absorbent Substances 0.000 title claims abstract description 15
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 title abstract description 16
238000002360 preparation method Methods 0.000 title description 2
238000006243 chemical reaction Methods 0.000 claims abstract description 17
239000000047 product Substances 0.000 claims abstract description 17
-1 cyano compound Chemical class 0.000 claims abstract description 13
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims abstract description 9
239000011261 inert gas Substances 0.000 claims abstract description 9
150000001875 compounds Chemical class 0.000 claims abstract description 8
239000007795 chemical reaction product Substances 0.000 claims abstract description 4
238000000034 method Methods 0.000 claims description 33
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
239000007789 gas Substances 0.000 claims description 13
150000001412 amines Chemical class 0.000 claims description 12
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 11
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 6
239000000376 reactant Substances 0.000 claims description 6
230000005587 bubbling Effects 0.000 claims description 5
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
239000000203 mixture Substances 0.000 claims description 2
239000011541 reaction mixture Substances 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
239000012736 aqueous medium Substances 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
238000009877 rendering Methods 0.000 claims 1
239000007864 aqueous solution Substances 0.000 abstract description 10
230000000694 effects Effects 0.000 abstract description 4
238000000746 purification Methods 0.000 abstract description 2
241000283984 Rodentia Species 0.000 abstract 1
VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 abstract 1
239000000243 solution Substances 0.000 description 12
150000004985 diamines Chemical class 0.000 description 10
238000010521 absorption reaction Methods 0.000 description 7
230000008929 regeneration Effects 0.000 description 7
238000011069 regeneration method Methods 0.000 description 7
LTYRAPJYLUPLCI-UHFFFAOYSA-N glycolonitrile Chemical compound OCC#N LTYRAPJYLUPLCI-UHFFFAOYSA-N 0.000 description 5
JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 5
239000007788 liquid Substances 0.000 description 5
238000002474 experimental method Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
DPUICVIJDAOKBK-UHFFFAOYSA-N 4-(2-hydroxyethyl)piperazin-2-one Chemical compound OCCN1CCNC(=O)C1 DPUICVIJDAOKBK-UHFFFAOYSA-N 0.000 description 3
238000007664 blowing Methods 0.000 description 3
229910001873 dinitrogen Inorganic materials 0.000 description 3
LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 3
BWKWNLMXXRCEPL-UHFFFAOYSA-N 1-(2-hydroxyethyl)piperazin-2-one Chemical compound OCCN1CCNCC1=O BWKWNLMXXRCEPL-UHFFFAOYSA-N 0.000 description 2
HXMVNCMPQGPRLN-UHFFFAOYSA-N 2-hydroxyputrescine Chemical compound NCCC(O)CN HXMVNCMPQGPRLN-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
PLKLFHFGLAWKAK-UHFFFAOYSA-N 1,4-bis(2-hydroxyethyl)piperazin-2-one Chemical compound OCCN1CCN(CCO)C(=O)C1 PLKLFHFGLAWKAK-UHFFFAOYSA-N 0.000 description 1
KOMFLBGACMTEAR-UHFFFAOYSA-N 1,4-dibutylpiperazin-2-one Chemical compound CCCCN1CCN(CCCC)C(=O)C1 KOMFLBGACMTEAR-UHFFFAOYSA-N 0.000 description 1
NFTWWHSKWXOTLL-UHFFFAOYSA-N 1,4-dimethylpiperazin-2-one Chemical compound CN1CCN(C)C(=O)C1 NFTWWHSKWXOTLL-UHFFFAOYSA-N 0.000 description 1
BSPUWRUTIOUGMZ-UHFFFAOYSA-N 3-methylpiperazin-2-one Chemical compound CC1NCCNC1=O BSPUWRUTIOUGMZ-UHFFFAOYSA-N 0.000 description 1
IIEAUKQEVCMTCY-UHFFFAOYSA-N 4-(2-hydroxybutyl)piperazin-2-one Chemical compound CCC(O)CN1CCNC(=O)C1 IIEAUKQEVCMTCY-UHFFFAOYSA-N 0.000 description 1
IXEQIZJFLXONEU-UHFFFAOYSA-N 4-(2-hydroxyethyl)-1-methylpiperazin-2-one Chemical compound CN1CCN(CCO)CC1=O IXEQIZJFLXONEU-UHFFFAOYSA-N 0.000 description 1
MLFYBQRWKLVYDG-UHFFFAOYSA-N 4-(2-hydroxyethyl)-5-methylpiperazin-2-one Chemical compound CC1CNC(=O)CN1CCO MLFYBQRWKLVYDG-UHFFFAOYSA-N 0.000 description 1
YODCUAYVOVZAMQ-UHFFFAOYSA-N 4-(2-hydroxypropyl)-6-methylpiperazin-2-one Chemical compound CC(O)CN1CC(C)NC(=O)C1 YODCUAYVOVZAMQ-UHFFFAOYSA-N 0.000 description 1
RNUOXYTZOTXYFD-UHFFFAOYSA-N 4-(2-hydroxypropyl)piperazin-2-one Chemical compound CC(O)CN1CCNC(=O)C1 RNUOXYTZOTXYFD-UHFFFAOYSA-N 0.000 description 1
KVIZTDNKHOCNAM-UHFFFAOYSA-N 4-methylpiperazin-2-one Chemical compound CN1CCNC(=O)C1 KVIZTDNKHOCNAM-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000006096 absorbing agent Substances 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
125000005263 alkylenediamine group Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
229940015043 glyoxal Drugs 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000005259 measurement Methods 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
- C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Gas Separation By Absorption (AREA)
Treating Waste Gases (AREA)
Hydrogenated Pyridines (AREA)

JP2266516A 1989-10-06 1990-10-05 二酸化硫黄吸収剤として用いるピペラジノンの製造方法 Pending JPH03135966A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US418292		1989-10-06
US07/418,292 US4980471A (en)	1989-10-06	1989-10-06	Preparation of piperazinones for use as sulfur dioxide absorbents

Publications (1)

Publication Number	Publication Date
JPH03135966A true JPH03135966A (ja)	1991-06-10

Family

ID=23657506

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP2266516A Pending JPH03135966A (ja)	1989-10-06	1990-10-05	二酸化硫黄吸収剤として用いるピペラジノンの製造方法

Country Status (12)

Country	Link
US (1)	US4980471A (fr)
EP (1)	EP0421794A3 (fr)
JP (1)	JPH03135966A (fr)
CN (1)	CN1050870A (fr)
AU (1)	AU6385390A (fr)
BR (1)	BR9005109A (fr)
CA (1)	CA2027107A1 (fr)
NO (1)	NO904336L (fr)
RO (1)	RO106738B1 (fr)
RU (1)	RU2036910C1 (fr)
YU (1)	YU187490A (fr)
ZA (1)	ZA907987B (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2049244A1 (fr) *	1990-08-16	1992-02-17	Steven H. Christiansen	Methode d'absorption de composes sulfures a partir de fluides grace a des composes heterocycliques renfermant au moins un atome d'azote cyclique
US5108723A (en) *	1990-08-16	1992-04-28	The Dow Chemical Company	Process for absorption of sulfur compounds from fluids
US5208363A (en) *	1990-10-15	1993-05-04	The Dow Chemical Company	Preparation of aminonitriles
US5191081A (en) *	1991-12-12	1993-03-02	W. R. Grace & Co.-Conn.	1-cyanomethyl-4-carboxymethyl-3-ketopiperazine, salts thereof and process for their preparation
US6461872B1 (en) *	1999-11-17	2002-10-08	General Electric Company	Poly(1,4-ethylene-2-piperazone) composition, method for production of a poly(1,4-ethylene-2-piperazone) composition, TCE-detecting method and sensor
CN115646137A (zh) *	2022-10-26	2023-01-31	北京北大先锋科技股份有限公司	一种有效减小发泡问题的有机胺脱硫剂

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2633467A (en) *	1952-02-08	1953-03-31	Rohm & Haas	N-hydroxyalkyl-2-ketopiperazines
US2700668A (en) *	1952-02-08	1955-01-25	Rohm & Haas	Preparation of ketopiperazines
US2649450A (en) *	1952-02-08	1953-08-18	Rohm & Hass Company	Preparation of 1,4-dialkyl-2-ketopiperazines
US4167512A (en) *	1977-09-21	1979-09-11	The B. F. Goodrich Company	Synthesis of 2-keto-1,4-diazacycloalkanes
US4170650A (en) *	1978-05-22	1979-10-09	The Dow Chemical Company	Oxopiperazinium salts, their preparation and their use
DE3119077A1 (de) *	1981-05-14	1982-12-02	Basf Ag, 6700 Ludwigshafen	Heterocyclische dihalogenacetmide, verfahren zu ihrer herstellung und herbizide mittel, die acetanilide als herbizide wirkstoffe und diese dihalogenacetamine als antagonistische mittel enthalten
US4530704A (en) *	1983-12-19	1985-07-23	The Dow Chemical Company	Selective absorption of SO2 from gases containing the same
US4767860A (en) *	1986-10-14	1988-08-30	The Dow Chemical Company	Preparation of N-substituted piperazinones
US4783327A (en) *	1987-08-13	1988-11-08	The Dow Chemical Company	Sulfur dioxide removal from gas streams using hydroxyalkyl substituted piperazinones
US4814443A (en) *	1987-08-13	1989-03-21	The Dow Chemical Company	Preparation of hydroxyalkylpiperazinones by reacting glyoxal with hydroxyalkyldiamines

1989
- 1989-10-06 US US07/418,292 patent/US4980471A/en not_active Expired - Fee Related
1990
- 1990-10-04 EP EP19900310892 patent/EP0421794A3/en not_active Withdrawn
- 1990-10-04 YU YU187490A patent/YU187490A/sh unknown
- 1990-10-04 RO RO146062A patent/RO106738B1/ro unknown
- 1990-10-05 NO NO90904336A patent/NO904336L/no unknown
- 1990-10-05 ZA ZA907987A patent/ZA907987B/xx unknown
- 1990-10-05 CN CN90108255A patent/CN1050870A/zh active Pending
- 1990-10-05 JP JP2266516A patent/JPH03135966A/ja active Pending
- 1990-10-05 AU AU63853/90A patent/AU6385390A/en not_active Abandoned
- 1990-10-05 RU SU904831352A patent/RU2036910C1/ru active
- 1990-10-05 CA CA002027107A patent/CA2027107A1/fr not_active Abandoned
- 1990-10-05 BR BR909005109A patent/BR9005109A/pt unknown

Also Published As

Publication number	Publication date
YU187490A (sh)	1992-09-07
EP0421794A3 (en)	1991-12-11
EP0421794A2 (fr)	1991-04-10
BR9005109A (pt)	1991-09-17
RO106738B1 (ro)	1993-06-30
NO904336D0 (no)	1990-10-05
AU6385390A (en)	1991-05-30
CA2027107A1 (fr)	1991-04-07
NO904336L (no)	1991-04-08
ZA907987B (en)	1992-06-24
RU2036910C1 (ru)	1995-06-09
CN1050870A (zh)	1991-04-24
US4980471A (en)	1990-12-25

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